1064
NOTES
significant in view of the fact that the time for Grignard formation was 2 hr. instead of 18 hr. with ether. I n a 5-1. three-necked flask, fitted with motor-driven stirrer, thermometer, and dropping funnel, were placed the following reactants: magnesium turnings (27 g., 1.1 g.atoma), sodium-dried tetrahydrofuran (tetrahydrofuran, distilled free from hydroquinone, 50 ml.), and methyl iodide (5 ml.). The mixture was gently warmed on the water bath until methylmagnesium iodide had formed. Tetrahydrofuran (150 ml.) was added and the mixture heated to gentle reflux. 4Bromophenoxytrimethylsilane (245 g., 1.0 mole) in tetrahydrofuran (400 ml.) was added dropwise with vigorous stirring over a 1-hr. period, after which the mixture was refluxed a further hour then cooled to 10". Trimethylchlorosilane (120 g., 1.1 moles) was added with stirring, the mixture was then brought to reflux for 1 hr., and allowed to cool overnight. The crystallized magnesium salts were dissolved in water (500 ml.), the tetrahydrofuran layer separated, washed four times with water, dried over anhydrous sodium sulfate, and distilled. The colorless liquid fraction of b.p. 132-135'/22-44 mm. was collected in 184 g. (77.4y0) yield. Refractionation yielded a liquid of b.p. 132-133"/25 mm., in agreement with the literature?value. 4-Trimethylsilylphenol. 111. 4Trimethylsilylphenoxytrimethylsilane (48.0 g., 0.2 mole) in 95% ethyl alcohol (15 ml.) was acidified with one drop of concd. hydrochloric acid then diluted with water (6 ml.). After shaking for 5 min., the mixture was diluted to turbidity with more water and then allowed to stand for 15 min. The lower aqueous layer was discarded and the organic layer was washed twice with 50ml. aliquots of water. The organic layer was transferred to a large dish and the alcohol allowed to evaporate in the air. 4-Trimethylsilylphenol rapidly crystallized in theoretical yield, m.p. 7 4 O , in agreement n
